Azo dye.



UNITED STATES PATENT OFFICE.

OscARcU 'rHER AND LEOPOLD nEssE, or ELBERFELRYHGRUANY, iss'ionons TFARBENFABRIKEN voni FRIEDR. BAYER & co, or ELBERFELD, GERMAN),

A CORPORATION OF GERMANY.

AZO

DYE.

Patented Jan. 28, 1908.

Application filed November 19. 1907. Serial No. 402-814- T 0 all whom itmay concern:

Be it known that we, OSCAR GI'JNTHER and LEUPOLD HEssE, doctors ofphilosophy, chemists, citizens of the German Empire, residing atElberield, Germany," Kingdom of Prussia, have invented new' and usefulImprovements in Azo Dyestuffs, of which the I following is aspecification.

Our invention relates to the manufacture and production of newdisazodyestufi's dyeihg cotton from bluish-red to violet to blue shadesremarkable for their fastness to light.

' They are obtained .by first producing intermediate compounds from thediazocompounds of 1. 8-aminonaphthol sulfonic acids with suitable amins,then diazotizing" these intermediate roductsv and combining the thusproduced some dyestuffs are obtained if'in the above mentioned processthe diazocompounds of 1.8 -aminonaphthol sulfonic acids are replaced. bythe d'iazocom ounds. of acidylized derivatives of these 'aci s e. g. bythe sulfur-. ous acid esters, the'acetyl derivatives or the a lsulfcnicacid esters. ofLS-aminonaphthol su fonic acids. The acid 1 groups suchas the sulfurous acid residue, t e acetyl or. arylsulfonic cups whichare attached to the hydroxy grou can be eliminated either from theinterme iate compounds or from the final dyestufl's. The presence of theacidyl groups in the hydr'onyl groups of'the aminonap obtained bytreating in an alkaline solution 1.8-aminona hthol sulfonic acid witharylsulfonic aci chlorids, e. g. benzene sulfonic-chlorid,toluenesulfonic chlorid, naphthalene sulfonic chlorid, etc.

The new dyestufis are in the shape of their alkaline salts dark' powderseasily soluble in water. Upon reductiomwith stannous chlorid andhydrochloric acid the dyestuiis are decomposed 1 .-8-aminonaphtholsulfonic acid. a diarnin and 2,fi-diamino-5-naphthol-7-sulfonic acid areformed.-

diazoazocompounds with 2- amino-5-naphthol-7-mono sulfonic acid. The 201.S-aminbnaphthol-3.(S-disulfonic acid aredissolved with the/necessaryquantity of sodium carbonate in Water to producea neutral solution. Itis then diazotized in the usual way with 69 parts of sodium nitrite andhydrochloric acid. The re'sultingdiazccompound is introddced into asolution of 1517 .5 parts of the hydrochlorid of para-xylidin in Wate'rand sodium acetate is added to neutralizethe free mineral acid.'lhe'mixture isacidiflated and the intermediate compound issalted out,filtered oii and conve ted into its neutral sodium salt. This is thendiazotized at about 5 (3. with 69 parts of sodium nitrite andhydrochloric acid and to remove any diazoxylidin if it should be presentthe diazocompound is salted out and filtered oil. It is then stirred uwith water to a paste and is added to a so ution of 239 parts of. 2-

an excess of sodium-carbonate. The commixture is gent salted out,filtered off and dried. t is after being dried and pulverized, in theshape of its sodium salt a dark powder which is soluble in water with aviolet; color an'd which is soluble in concentrated sulfuric acid with agreenish-blue color. By reduction with stannous chl'orid andhydrochloric acid 1.8- aminonaphthol 3.6-disulfonic acid,2.5-(liamino-1.4-dimethylben'zcne and 2.6-diamino-5-11aphthol-T-sulfonic acid are obtained. The new .dyestufl' dyes cottonreddish-violet shades.

In the following table the shades of of the new dyes are given:

Dycsi uil' obtained from:

1) I-B-aminonaphihol-fML-disulfonic aclrl-hcrcsiviolet.

din+2.5-a|ninonaphthol-7-sulionic acid 2 LS-aminonaphthoi-fLU-disullonicacid+metareddish-viotoluidin+2;5-aminonaphth0l-7-sulionlc acid let2.5-aminonaphthol-T-sulionic acid 3) Ls-aminonaphthoHfl-disulionicacid+cresiviolet-blue. d in+2.5-aminonaphthol-7-sulfonic acid 4l.8-21minonaphthol-3.5-disulionic aeid+crr.-sireddish-blue.

- din+2.5-aminonaphthol-I-suifonic acid 5 1.S-aminonaphthol-o-suiionioacid+cresidin+ violet. v

2.5-aminonaphthol-7-sull'onie acid I I I 6 1.X-aminonaphthol-S-suiionicacid+eresldln+ bluish-violet.

in an analogous manner on using other 1.8-

amino-5-naphthol-7-sull onic acid containing.

bination is complete after a short time. The a y heated and the d estuifissome Dyes cottonz' The above described process is carried outaminonaph'tholsulfonic acids, or other suitable amins at g. alphanaphthylamin etc. to produce the intermediate compounds capale of beingdiazotized. I

Having now described our invention and in what manner the same is to beperformed, What W6 claim as new and desire to secure by Letters Patentis 1. The herein-described new azo-dyestufl's obtainable by combiningthe diazocom-g pounds of 1.8-aminonaphthol sulfonic acids with suitableamins, then diazotizing these intermediate compounds and combining the 1thus produced diazqazocompounds with 2- amino-5-naphthol-7-sulfonicacid, which dyestuffs are, after being dried and pulverized,

in the shape of their alkaline salts, dark powders easily solubleinwater; yielding u )OIl 1 reduction with stannous chlorid and by 10-chloric acid 1.8-aminonaphthol sulfonic acid, E

,a diamin and 2.6-diaInino-5-na )hthol-,7-sul- "ionic acid, dyeingcotton from luish-red to violet t0 blue shades, substantially ashereinbefore described.

2k 2. The herein-described new azo-dyestufi,

emcee which can-I be obtained" by combining the diazocompound of1.8-aminonaphthol-8'.6- disulfonic acid with paraxylidin, diazotizing'the intermediate compound thus produced ble in concentrated sulfuricacid with a greenish-blue color; yielding u on reduction with stannouschlorld and hyr IQClllOI'lC acid with: $0

1.8-aminonaphthol-3.G-disultonic acid, 2.5-

diamino-l .4-dimethylbcnzene, and 2,6 di-' an1ino 5-naphtliol-7-sulfonic"acid; and dyein" cottonViolct-red shades, substantially, 1

h as herelnbefore described.

In testimony whereof we have hereunto set our hands in the presence oftwo -subscribing witnesses. 1 7

OSCAR GUNTHER. [1,. s.] LEOPOLD HESSPL [1.1.8.] Witnesses l (yrro Kome,

WM. W'AsHINGTON BRUNSWICK.

